Water → HCID 59506799, compound

HRID 1261137Notes

Reaction equation

HRID 1261137 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-8e8f27fee3cc48a1a28e4a0667b67618
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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