Water → HCID 71295475, compound

HRID 1776807Notes

Reaction equation

HRID 1776807 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[C:15]([F:18])[CH:14]=[CH:13][CH:12]=3)[CH:3]=1.[C:19]([O-])([O-])=O.[K+].[K+].C(Br)Br.O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:19][N:10]3[C:11]4[CH:12]=[CH:13][CH:14]=[C:15]([F:18])[C:16]=4[CH:17]=[C:9]3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 71295472HCID 71295472, compound

Product 1

HCID 71295475HCID 71295475, compoundYield 121.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-2-(4-fluoro-1H-indol-2-yl)phenol (40 mg, 0.15 mmol) in DMF (1 mL), K2CO3 (40 mg, 0.31 mmol) and CH2Br2 (53 mg, 0.31 mmol) were added at 25° C. The mixture was stirred at 80° C. for 2 hours, and cooled to 25° C. H2O (50 mL) was added, then the mixture was extracted with ethyl acetate and washed with brine, dried over Na2SO4. After concentrated, the resulting residue was purified using prep-TLC (petroleum ether:EtOAc=10:1) to provide the product of 2-chloro-11-fluoro-6H-benzo[5,6][1,3]oxazino[3,4-a]indole (50 mg, yield: 45%). 1H-NMR (CDCl3, 400 MHz) δ 7.68 (s, 1H), 7.14˜7.23 (m, 2H), 7.03˜7.09 (m, 2H), 6.90 (s, 1H), 6.81˜6.86 (m, 1H), 5.88 (s, 2H). MS (M+H)+: 274/276.

Workup

  1. temperaturecooled to 25° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentrated
  6. customthe resulting residue was purified

Sources & evidence

ORD record
ord-43ff65568c2943aeb26c1ac818f05088
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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