3-Bromoaniline → 4-(3-Bromoanilino)indolo[2,3-d]pyrimidine hydrochloride

HRID 1489608Notes

Reaction equation

HRID 1489608 reaction equation
Cl.[Cl:2][C:3]1[C:4]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>C(O)C>[ClH:2].[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH:20][C:3]1[C:4]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 181843914-Chloroindolo[2,3-d]pyrimidine hydrochloride

Product 1

HCID 181844134-(3-Bromoanilino)indolo[2,3-d]pyrimidine hydrochlorideYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloroindolo[2,3-d]pyrimidine hydrochloride (240 mg, 1 mmol) and 3-bromoaniline (0.33 mL, 3 mmol) in ethanol (3 mL) are heated under reflux for 2h. The solids are collected by suction filtration, washed with ethanol and dried to give 4-(3-bromoanilino)indolo[2,3-d]pyrimidine hydrochloride (248 mg, 73%). 1H NMR (DMSO) δ1H, s), 9.02 (1H, s),8.51 (1H, s), 8.42 (1H, d, J=7.7 Hz), 8.08 (1H, t, J=1.9 Hz), 7.82 (1H, d, J=8.0 Hz), 7.53 (1H, d, J=7.9 Hz), 7.46 (1H, dr, Jd =1.0 Hz, Jt =7.6 Hz), 7.36-7.27 (3H, m). ##STR29##

Workup

  1. temperatureunder reflux for 2h
  2. filtrationThe solids are collected by suction filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-11f094e40b19467ead52d7fcab7bdb90
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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