Triphenylphosphine → HCID 90111932, compound

HRID 1051407Notes

Reaction equation

HRID 1051407 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[F:18])[NH:14][N:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[F:18])[N:14]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=1[CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)[N:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 59151432HCID 59151432, compoundHCID 90111076HCID 90111076, compound

Product 1

HCID 90111932HCID 90111932, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(benzylthio)-6-fluoro-1H-indazole (1-2, 0.35 g, 1.35 mmol, 1.0 equiv) and tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.53 g, 2.03 mmol, 1.5 equiv) in THF (6.77 mL) at 0° C. was added polymer supported triphenylphosphine (0.71 g, 2.71 mmol, 2.0 equiv) followed by di-tertbutylazodicarboxylate (0.62 g, 2.71 mmol, 2.0 equiv) and the reaction mixture was stirred at 0° C. for 2.5 hours. The reaction was concentrated and purified using normal phase chromatography to yield the desired regioisomer. ESI+ MS [M+H]+ C29H30FN3O2S: 504.3 found, 504.6 required.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified
  3. customto yield the desired regioisomer

Sources & evidence

ORD record
ord-897f6eb501674c569c5fd8c99d13975c
Source dataset
uspto-grants-2016_07
Patent number
US09388179B2

Reaction notes

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