Formic Acid → HCID 131731728, compound

HRID 2401145Notes

Reaction equation

HRID 2401145 reaction equation
C(O)=O.[C:4]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]3[N:16]=[C:17]([O:27][C:28]4[CH:29]=[CH:30][C:31]([CH3:38])=[C:32]([CH:37]=4)[C:33]([O:35][CH3:36])=[O:34])[N:18](COCC[Si](C)(C)C)[C:13]3=[CH:12][C:11]=2[Cl:39])=[CH:6][CH:5]=1.S(=O)(=O)(O)[O-].[K+]>>[C:4]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[C:14]3[N:16]=[C:17]([O:27][C:28]4[CH:29]=[CH:30][C:31]([CH3:38])=[C:32]([CH:37]=4)[C:33]([O:35][CH3:36])=[O:34])[NH:18][C:13]3=[CH:12][C:11]=2[Cl:39])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 516920Potassium bisulfateHCID 89557991HCID 89557991, compound

Product 1

HCID 131731728HCID 131731728, compound

Procedure

A formic acid (2.7 mL, 70.4 mmol) solution of methyl 5-{[5-(biphenyl-4-yl)-6-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H imidazo[4,5-b]pyridin-2-yl]oxy}-2-methylbenzoate (140 mg, 0.23 mmol) and saturated potassium bisulfate (0.27 mL) was stirred at 80° C. for 1 h. The reaction was partitioned between EtOAc and brine. The organic layer was separated, and concentrated to give methyl 5-{[5-(biphenyl-4-yl)-6-chloro-1-H imidazo[4,5-b]pyridin-2-yl]oxy}-2-methylbenzoate as a white solid, which was used in the next step without further purification. LC-MS: calculated for C27H20ClN3O3 456.89, observed m/e: 470.2 (M+H)+ (Rt 2.3/4 min).

Workup

  1. customThe reaction was partitioned between EtOAc and brine
  2. customThe organic layer was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-891150cd45ae4dc7828cc38f45e160bd
Source dataset
uspto-grants-2014_08
Patent number
US08796258B2

Reaction notes

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