Ethyl chloroformate → HCID 59374990, compound

HRID 661946Notes

Reaction equation

HRID 661946 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:26]2[C:25]3[C:20](=[CH:21][C:22]([OH:27])=[CH:23][CH:24]=3)[NH:19][C:18]=2[C:17]([C:28]([NH2:30])=[O:29])=[CH:16][CH:15]=1>N1C=CC=CC=1.CCOC(C)=O>[C:2](=[O:3])([O:4][CH2:5][CH3:6])[O:27][C:22]1[CH:23]=[CH:24][C:25]2[C:26]3[C:18](=[C:17]([C:28](=[O:29])[NH2:30])[CH:16]=[CH:15][C:14]=3[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[F:7])[NH:19][C:20]=2[CH:21]=1

Participants

5

Reactant 2

HCID 10928Ethyl chloroformate3×HCID 59375146HCID 59375146, compound

Product 1

HCID 59374990HCID 59374990, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl chloroformate (8.19 mg, 0.075 mmol) was added to a solution of 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide (Example 40-1, 18.6 mg, 0.058 mmol) in pyridine (1 mL). After 17 h, additional ethyl chloroformate (8.19 mg, 0.075 mmol) was added. After 5 h more, additional ethyl chloroformate (0.05 mL) was added. After 15 h more, the mixture was diluted with EtOAc (30 mL), washed with water (10 mL) and brine (5 mL), dried and concentrated. The residue was purified by preparative HPLC to provide 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazol-2-yl ethyl carbonate as a white solid (7.0 mg, 28%). 1H NMR (400 MHz, chloroform-d) δ 10.44 (1H, br. s.), 7.62 (1H, dd, J=7.92, 1.98 Hz), 7.41-7.57 (2H, m), 7.20-7.40 (4H, m), 7.16 (1H, dd, J=7.81, 1.65 Hz), 6.79-6.92 (1H, m), 6.60 (2H, br. s.), 4.34 (2H, q, J=7.26 Hz), 1.41 (3H, t, J=7.15 Hz). Mass spectrum m/z 393.0 (M+H)+.

Workup

  1. waitAfter 5 h more
  2. waitAfter 15 h more
  3. washwashed with water (10 mL) and brine (5 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7756de87df1c4f29aca194ac4ad3bb3d
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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