2-Furancarbonyl chloride → HCID 90403260, compound

HRID 589805Notes

Reaction equation

HRID 589805 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=3[Cl:18])[NH2:14])=[N:8][C:5]2=[N:6][CH:7]=1.[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](Cl)=[O:25]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:12]=[C:13]([NH:14][C:24]([C:20]4[O:19][CH:23]=[CH:22][CH:21]=4)=[O:25])[CH:15]=[CH:16][C:17]=3[Cl:18])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 61676010HCID 61676010, compound

Product 1

HCID 90403260HCID 90403260, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-[6-bromo-1H-imidazo[4,5-b]pyridin-2-yl]-4-chloroaniline (15 g, 46.36 mmol, 1.00 equiv) in dichloromethane (150 mL) was added furan-2-carbonyl chloride (9.1 g, 69.72 mmol, 1.50 equiv) in a bath of ice and stirred overnight at room temperature. The reaction was then quenched by the addition of 50 mL of methanol and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/2) to give 8.9 g (46%) of N-(3-[6-bromo-1H-imidazo[4,5-b]pyridin-2-yl]-4-chlorophenyl)furan-2-carboxamide (I-2) as a light yellow solid. 1H-NMR: (DMSO, 300 MHz): 13.09-13.79 (m, 1H), 10.53 (s, 1H), 8.51 (s, 1H), 8.36 (brs, 2H), 7.98-8.02 (m, 2H), 7.68 (d, J=9.0 Hz, 1H), 7.40 (d, J=3.3 Hz, 1H), 6.74 (dd, J=3.3, 1.8 Hz, 1H). MS M/Z=419 (M+1).

Workup

  1. customThe reaction was then quenched by the addition of 50 mL of methanol
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dbd6d34fb2324cf6b6be78a88be02600
Source dataset
uspto-grants-2016_01
Patent number
US09233961B2

Reaction notes

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