Water → HCID 59506799, compound

HRID 1098498Notes

Reaction equation

HRID 1098498 reaction equation
[CH:1]([Si:4]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)=[CH:6]1)([CH3:3])[CH3:2].[F:28][C:29]([F:40])([F:39])[C:30]1[CH:31]=[C:32]([N:36]=[C:37]=[O:38])[CH:33]=[CH:34][CH:35]=1.C(N(CC)CC)C.O>O1CCCC1>[F:28][C:29]([F:39])([F:40])[C:30]1[CH:31]=[C:32]([NH:36][C:37]([NH:21][C:18]2[CH:17]=[CH:16][C:15]([CH2:14][C:7]3[C:8]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[N:5]([Si:4]([CH:1]([CH3:2])[CH3:3])([CH:22]([CH3:24])[CH3:23])[CH:25]([CH3:27])[CH3:26])[CH:6]=3)=[CH:20][CH:19]=2)=[O:38])[CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 58087581HCID 58087581, compound

Product 1

HCID 59506799HCID 59506799, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-phenylamine (113, 70.0 mg, 0.184 mmol) was dissolved in tetrahydrofuran (12 mL) and 3-trifluoromethyl-phenyl isocyanate (41 mg, 0.22 mmol) and triethylamine (28 mg, 0.28 mmol) were added under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature overnight, then poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated to give crude compound 114 used in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-11ffeef3c4d84221bd86669980b96a35
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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