Triphenylphosphine → HCID 53909999, compound

HRID 1275055Notes

Reaction equation

HRID 1275055 reaction equation
[CH:1]12[N:7]([C:8](=[O:48])[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][C:16]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=3)=[C:15]4[C@H:29]([CH3:47])[CH2:30][NH:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=3[N+:44]([O-:46])=[O:45])(=[O:34])=[O:33])([CH3:11])[CH3:10])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[N:49]1[C:57]2[C:52](=[N:53][CH:54]=[CH:55][CH:56]=2)[N:51]([CH2:58][CH2:59]O)[CH:50]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[CH:4]12[N:7]([C:8](=[O:48])[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][C:16]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=3)=[C:15]4[C@H:29]([CH3:47])[CH2:30][N:31]([CH2:59][CH2:58][N:51]3[C:52]4=[N:53][CH:54]=[CH:55][CH:56]=[C:57]4[N:49]=[CH:50]3)[S:32]([C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=3[N+:44]([O-:46])=[O:45])(=[O:33])=[O:34])([CH3:10])[CH3:11])[CH:1]([CH2:2][CH2:3]1)[CH2:6][CH2:5]2

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22715675HCID 22715675, compoundHCID 54478802HCID 54478802, compound

Product 1

HCID 53909999HCID 53909999, compoundYield 299.4%

Procedure

To a solution of (S)-N-{2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-propyl}-2,4-dinitrobenzenesulfonamide (0.415 g in 6 mL benzene) was added 0.20 g 2-imidazo[4,5-b]pyridin-3-yl-ethanol followed by 0.32 g triphenylphosphine and 0.189 mL of diethyl azodicarboxylate added dropwise. After 2 hours, the mixture was concentrated and the crude reaction product purified by flash chromatography on silica gel (methylene chloride:methanol, 98:2; then 95:5) to give the title compound (1.51 g).

Workup

  1. additionadded dropwise
  2. concentrationthe mixture was concentrated
  3. customthe crude reaction product
  4. custompurified by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-325b5317c4fb45df8f775f05b67a65ad
Source dataset
uspto-grants-2000_12
Patent number
US06159975

Reaction notes

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