1-(5-Bromopyridin-2-yl)-1H-pyrazole synthesis
- Product Name:1-(5-Bromopyridin-2-yl)-1H-pyrazole
- CAS Number:433922-57-7
- Molecular formula:C8H6BrN3
- Molecular Weight:224.06
288-13-1
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624-28-2
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433922-57-7
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$64.53/0.5g
Yield:433922-57-7 89%
Reaction Conditions:
Stage #1: NH-pyrazolewith sodium hydride in N,N-dimethyl-formamide at 10 - 20; for 0.5 h;
Stage #2: 2,5-dibromopyridine in N,N-dimethyl-formamide at 20 - 70;
Steps:
5-Bromo-2-(1H-pyrazol-1-yl)pyridine (6)
Pyrazole (5)(6.5 g, 0.0949 mol) in DMF (30 mL) was added slowly to asolution of NaH (2.28 g, 0.0949 mol) in DMF (1.0 L) at10 °C and allowed for stirring at room temperature for 0.5 h.The reaction mass was cooled to 10 °C. To the abovereaction mass, 2,5-Dibromo pyridine (4) (15 g, 0.0633 mol)was added and the reaction mixture was allowed for stirringat room temperature for 1 h. Furthermore, the reaction masswas again heated to 70 °C for 3 h until the total consumptionof the starting material. The reaction mass was thenadded to 100 mL ice-cold water when the product precipitatedas a white solid 6 in 12.4 g with 89% yield. MP:69-70 °C. IR (KBr): 3059, 823, 751, 672 cm-1; 1H NMR(400 MHz, CDCl3): δ 6.45 (t, 1H), 7.72 (d, 1H, J = 0.4 Hz),7.86-7.88 (m, 2H), 8.42 (d, 1H, J = 1.2 Hz), 8.49 (d, 1H,J = 2.4 Hz); 13C NMR (100 MHz, CDCl3): δ 108.1, 113.8,117.2, 127.1, 141.3, 142.4, 148.9, 150.3; MS (ESI): m/z:224 [M+2]+; Anal. Calcd for C8H6BrN3: C, 42.88; H, 2.70;N, 18.75. Found: C, 42.74; H, 2.62; N, 18.89.
References:
Rani, Chekuri Sharmila;Reddy, Alugubelli Gopi;Susithra;Mak, Kit-Kay;Pichika, Mallikarjuna Rao;Reddymasu, Sreenivasulu;Rao, Mandava Venkata Basaveswara [Medicinal Chemistry Research,2021,vol. 30,# 1,p. 74 - 83]
288-13-1
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380380-69-8
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433922-57-7
32 suppliers
$64.53/0.5g
624-28-2
716 suppliers
$5.00/5g
433922-57-7
32 suppliers
$64.53/0.5g
288-13-1
414 suppliers
$10.00/1g
1043906-08-6
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433922-57-7
32 suppliers
$64.53/0.5g
766-11-0
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$6.00/5g
433922-57-7
32 suppliers
$64.53/0.5g