3-Bromoaniline → HCID 18184420, compound

HRID 1358287Notes

Reaction equation

HRID 1358287 reaction equation
Cl.[Cl:2][C:3]1[C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[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[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 181843684-Chloro-5H-pyrimido[5,4-b]indole--hydrogen chloride (1/1)

Product 1

HCID 18184420HCID 18184420, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Choroindolo[3,2-d]pyrimidine hydrochloride (240 mg, 1 mmol) and 3-bromoaniline (0.33 mL, 3 mmol) in ethanol (3 mL) are heated at reflux under a nitrogen atmosphere for 2 h. Filtration and washing of the collected solids with ethanol, followed by recrystallization from DMF gives 4-(3-bromoanilino)indolo[3,2-d]pyrimidine hydrochloride (288 mg, 77%). 1H NMR (DMSO) δ12.73 (1H, s), 11.42 (1H, s), 9.02 (1H, s), 8.41 (1H, s), 8.28 (1H, d, J=7.9 Hz), 7.95-7.92 (1H, m), 7.84-7.82 (1H, d, J=8.6 Hz), 7.74-7.69 (1H, m), 7.40-7.47 (3H, m).

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 2 h
  2. filtrationFiltration
  3. washwashing of the collected solids with ethanol
  4. customfollowed by recrystallization from DMF

Sources & evidence

ORD record
ord-d96137085f0d436a96150d8698676622
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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