Dichloromethane → HCID 21882307, compound

HRID 1977240Notes

Reaction equation

HRID 1977240 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=1)=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)[Cl:33]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=1)=[C:12]2[Cl:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 21882255HCID 21882255, compound

Product 1

HCID 21882307HCID 21882307, compoundYield 78%

Conditions

Temperature
0 °C

Procedure

A flask was charged with 5-benzyloxy-2-(4-benzyloxy-phenyl)-1 H-indole No. 141 (8.0 g, 20.0 mmole) and CH2Cl2 (50 ml). The reaction was cooled to 0° C. and n-chlorosuccinimide (2.9 g, 22 mmole) was added. The reaction was stirred at 0° C. for 20 min. The reaction was then washed with 10% sodium sulfit solution, dried over MgSO4, and concentrated. To the resulting brown solid was added MeOH and the mixture was stirred for 15 min. The solid was filtered to give 6.8 g of a tan solid (78%). Mp=157-160° C.; 1H NMR (DMSO) 11.5 (s, 1 H), 7.80 (d, 2 H, J=7.0 Hz), 7.42−7.28 (m, 11 H), 7.17 (d, 2 H, J=8.7 Hz), 7.01 (d, 1 H, J=2.2 Hz), 6.88 (dd, 1 H, J=8.8 Hz, J=2.4 Hz), 5.17 (s, 2 H), 5.13 (s, 2 H); MS eI m/z 439 (M+).

Workup

  1. washThe reaction was then washed with 10% sodium sulfit solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. additionTo the resulting brown solid was added MeOH
  5. stirringthe mixture was stirred for 15 min
  6. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-71f422f5f23c4bc9af4232cfbcbf646d
Source dataset
uspto-grants-2001_05
Patent number
US06232307B1

Reaction notes

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