Water → HCID 58948674, compound

HRID 1509652Notes

Reaction equation

HRID 1509652 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[OH:14].[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:21]([O:14][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH:1]=1)[C:18]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 935512-Hydroxycarbazole

Product 1

HCID 58948674HCID 58948674, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9H-carbazol-2-ol (8.57 g, 46.78 mmol, 1.0 eq), BnBr (5.56 mL, 46.78 mmol, 1.0 eq) and K2CO3 (6.47 g, 46.78 mmol, 2.0 eq) in DMF (70 mL) was stirred at room temperature for two days. Then water (70 mL) was added, the mixture was stirred at room temperature for another 5 minutes. The precipitate was filtered and washed with water three times first, then washed with ethyl acetate once. The collected solid was dried in air under reduced pressure to afford the desired product as a grey solid (10.68 g in 83% yield). 1H NMR (DMSO-d6, 400 MHz): δ 5.21 (s, 2H), 6.86 (dd, J=7.2, 2.0 Hz, 1H), 7.06 (d, J=1.6 Hz, 1H), 7.10-7.13 (m, 1H), 7.28-7.31 (m, 1H), 7.35 (t, J=6.0 Hz, 1H), 7.40-7.44 (m, 3H), 7.52 (d, J=5.6 Hz, 2H), 7.97-8.00 (m, 2H), 11.12 (s, 1H).

Workup

  1. stirringthe mixture was stirred at room temperature for another 5 minutes
  2. filtrationThe precipitate was filtered
  3. washwashed with water three times first
  4. washwashed with ethyl acetate once
  5. customThe collected solid was dried in air under reduced pressure

Sources & evidence

ORD record
ord-3bea4bdd83e544928318b17de7aad921
Source dataset
uspto-grants-2015_12
Patent number
US09224963B2

Reaction notes

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