Isobutyl chloroformate → HCID 86642957, compound

HRID 1811135Notes

Reaction equation

HRID 1811135 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([C:18]([OH:20])=O)[CH2:8][C:9]=1[NH:10]2.ClC(OCC(C)C)=O.Cl.[CH3:30][NH:31][O:32][CH3:33]>C1COCC1.O.C(Cl)Cl>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:16])=[O:17])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([C:18]([N:31]([O:32][CH3:33])[CH3:30])=[O:20])[CH2:8][C:9]=1[NH:10]2

Participants

7

Reactant 3

HCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 66606746HCID 66606746, compound2×

Product 1

HCID 86642957HCID 86642957, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Step 1 A solution of 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid (Intermediate 49-3, 2 g, 5.93 mmol) and TEA (2.067 mL, 14.83 mmol) in THF (20 mL) was treated with isobutyl chloroformate (0.810 g, 5.93 mmol) at 0° C. The mixture was stirred for 10 min, then was treated with a solution of N,O-dimethylhydroxylamine hydrochloric acid salt (0.579 g, 5.93 mmol) in THF (2 mL) and water (1 mL). The mixture was stirred at 0° C. for 1 h, then was diluted with DCM, washed with NaHCO3 (aq) and water, dried and concentrated. The residue was triturated with DCM to provide 5-bromo-N2-methoxy-N2-methyl-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide as a light yellow solid (1.73 g, 77%). Mass spectrum m/z 380, 382 (M+H)+.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. washwashed with NaHCO3 (aq) and water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was triturated with DCM

Sources & evidence

ORD record
ord-7788d15c5ed943f1950e92bf61fccc24
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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