Water → HCID 59232072, compound

HRID 1099292Notes

Reaction equation

HRID 1099292 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]4[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=4[F:34])=[O:22])=[C:16]([F:35])[CH:15]=3)[CH:9]=[C:10]([CH2:11][CH2:12]O)[N:6]2[N:5]=[CH:4][N:3]=1.C(Br)(Br)(Br)[Br:37].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]4[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=4[F:34])=[O:22])=[C:16]([F:35])[CH:15]=3)[CH:9]=[C:10]([CH2:11][CH2:12][Br:37])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59232033HCID 59232033, compound

Product 1

HCID 59232072HCID 59232072, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-{4-[4-amino-7-(2-hydroxyethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]-2-fluorophenyl}-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea (1.28 g, 2.60 mmol) in anhyrous THF (32 ml) at 0° C. was added CBr4 (1.03 g, 3.1 mmol)) followed by Ph3P (0.75 g, 2.9 mmol) and the reaction was stirred at rt for 24 h. The reaction mixture was poured into H2O (100 ml) and extracted with 150 ml EtOAc. The organic layer was washed with satd. aq NaHCO3, brine and dried over Na2SO4 and was concentrated to give a yellow oil (1.6 g), which was used without further purification. MS [M+H]+=557.2; LCMS RT=3.27 min.

Workup

  1. extractionextracted with 150 ml EtOAc
  2. washThe organic layer was washed with satd
  3. dry with materialaq NaHCO3, brine and dried over Na2SO4
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-3a9b29715e7b43f2bee69af1952998fc
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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