Carbon Tetrachloride → HCID 58148079, compound

HRID 1879924Notes

Reaction equation

HRID 1879924 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]3[C:32]([Br:33])=[CH:31][C:30]([N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[CH:29][N:17]3[C:18](=[O:28])[C:19]=2[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:13])=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[CH2:21]([O:20][C:19]1[C:18](=[O:28])[N:17]2[CH:29]=[C:30]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)[CH:31]=[C:32]([Br:33])[C:16]2=[N:15][C:14]=1[C:12]1[O:13][C:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:10][N:11]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66953351HCID 66953351, compound

Product 1

HCID 58148079HCID 58148079, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of example 2 (140 mg, 0.23 mmol) in acetonitrile (2 ml), carbon tetrachloride (213 mg, 1.383 mmol), triethylamine (117 mg, 1.1584 mmol) and triphenylphosphine (302 mg, 1.151 mmol) were added successively at room temperature. The mixture was stirred for 3 hours. The product was purified by column chromatography (CH2Cl2/MeOH=150/1) to give the titled compound (25 mg, 20% yield).

Workup

  1. customThe product was purified by column chromatography (CH2Cl2/MeOH=150/1)

Sources & evidence

ORD record
ord-551498e9240649f5a9ce81185fd496e6
Source dataset
uspto-grants-2012_11
Patent number
US08318732B2

Reaction notes

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