HCID 10270183, compound → HCID 10114380, compound

HRID 1271129Notes

Reaction equation

HRID 1271129 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[N:7]([C:12]1[CH:17]=[C:16]([NH:18][CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[N:15]=[C:14]([CH3:24])[N:13]=1)[CH2:6][CH2:5]2.[Br-:25].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:25][C:17]1[C:12]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=3[Cl:11])[CH2:5][CH2:6]2)=[N:13][C:14]([CH3:24])=[N:15][C:16]=1[NH:18][CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 10270183HCID 10270183, compoundHCID 21124087Pyridiniumtribromide

Product 1

HCID 10114380HCID 10114380, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-2-methylpyrimidine (1.15 g, 3.14 mmol) and pyridinium tribromide (1.16 g, 3.63 mmol) were stirred in dry dichloromethane (20 mL) at 20° C. for 16 h. The reaction mixture was quenched with saturated aqueous Na2S2O5 (6 mL) and diluted with EtOAc (200 mL). The EtOAc was washed with water, brine, dried and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes to give the product, 5-bromo-4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-2-methylpyrimidine (1.30 g, 93% yield).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous Na2S2O5 (6 mL)
  2. additiondiluted with EtOAc (200 mL)
  3. washThe EtOAc was washed with water, brine
  4. customdried
  5. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-0a6a696e42654ddc95fbbac178d9df0d
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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