1,1'-Carbonyldiimidazole → HCID 71295693, compound

HRID 1776822Notes

Reaction equation

HRID 1776822 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:15]=1>CN(C1C=CN=CC=1)C.ClCCl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]2[O:20][C:1](=[O:2])[N:22]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[CH:29]=[C:21]3[C:16]=2[CH:15]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 13163448HCID 13163448, compound

Product 1

HCID 71295693HCID 71295693, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Carbonyldiimidazole (490 mg, 2 mmol) and DMAP (50 mg) were added to a solution of 4-bromo-2-(1H-indol-2-yl)phenol (576 mg, 2 mmol) in 20 mL of dichloromethane and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane, washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane/EtOAc 20:1) provided 2-bromo-6H-benzo[5,6][1,3]oxazino[3,4-a]indol-6-one as light yellow powder (500 mg, 79.6%). 1H-NMR (CDCl3, 400 MHz) δ 8.49 (d, J=8.4 Hz, 1H), 7.96 (s, 1H), 7.70 (d, J=7.2 Hz, 1H), 7.41˜7.53 (m, 3H), 7.22 (d, J=8.8 Hz, 1H), 7.07 (s, 1H). MS (M+H)+: 314/316.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (hexane/EtOAc 20:1)

Sources & evidence

ORD record
ord-e3f114d7f0994dbea2155128ca487bbe
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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