Tri-o-tolylphosphine → 3-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-carbamoylphenyl)-1H-indole

HRID 1441073Notes

Reaction equation

HRID 1441073 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Sn](CCCC)(CCCC)CCCC)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2].[CH2:23]([O:30][C:31]([N:33]1[CH2:37][CH2:36][CH2:35][C@@H:34]1[CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45](Br)[CH:46]=2)[NH:41][CH:40]=1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH2:23]([O:30][C:31]([N:33]1[CH2:37][CH2:36][CH2:35][C@@H:34]1[CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[O:3])[NH2:2])[CH:5]=3)[CH:46]=2)[NH:41][CH:40]=1)=[O:32])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 224209363-Carbamoylphenyltri-n-butylstannaneHCID 22859561(R)-Benzyl 2-((5-bromo-1H-indol-3-yl)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 228595563-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-carbamoylphenyl)-1H-indoleYield 30.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

3-carbamoylphenyltri-n-butylstannane (3.076 g, 7.50 mmol) (see Preparation 9) and 3-(1-benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-bromo-1H-indole (2.81 g, 6.80 mmol) (see Preparation 35B) were reacted together in the presence of tri-o-tolylphosphine, triethylamine and palladium (II) acetate using a procedure similar to that described in Example 1. This yielded the title compound as a pale yellow foam (954 mg). Found: C,68.45; H,5.92; N,8.10; C28H27N3O3. 7/12CH2Cl2 requires: C,68.24; H,5.64; N,8.35%.

Sources & evidence

ORD record
ord-89d6d333e7fb43dda26670a02fc5c195
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

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