Potassium Carbonate → HCID 58677613, compound

HRID 1012632Notes

Reaction equation

HRID 1012632 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])=[O:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35]>C(Cl)Cl>[CH2:37]([O:36][C:34](=[O:35])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8](=[O:9])[C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])[CH:7]=1)[CH:38]=[CH2:39]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18052Allyl chloroformateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677613HCID 58677613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 494 (0.06 g, 0.16 mmol) was suspended in dry CH2Cl2 (1.5 mL) under an argon atmosphere in a screw cap vessel. K2CO3 (0.044 g, 0.32 mmol) was added followed by allyl chloroformate (0.034 mL, 0.032 mmol). The suspension was stirred for 48 h at room temperature. Work up as described in the preparation of compound 277. The crude product was purified by flash chromatography using a gradient of EtOAc/petroleum ether (40-60) 5:95→30:70 as the eluent. This afforded the title compound as yellow oil. 13C NMR (CDCl3) δ 195.8, 159.1 (dd), 155.5 (dd), 153.2, 147.7, 139.6, 135.4, 135.2, 133.6, 132.9, 132.3, 132.0, 129.3, 124.4 (dd), 124.2 (dd), 121.3, 119.7, 118.3, 116.3, 112.8, 111.6 (dd), 105.0 (dd), 65.9, 19.7

Workup

  1. customcap vessel
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-383e0d9b825847459877249500f60791
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

Loading…