5-Bromoindole → (R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole

HRID 1182390Notes

Reaction equation

HRID 1182390 reaction equation
CN1[C@@H](CC2C3C=C(CCS(C4C=CC=CC=4)(=O)=O)C=CC=3NC=2)CCC1.C1(S(C=CC2C=C3C(=CC=2)NC=C3C[C@H]2CCCN2C)(=O)=O)C=CC=CC=1.BrC1C=C2C(=CC=1)NC=C2.C(O[C:73]([N:75]1[CH2:79][CH2:78][CH2:77][C@@H:76]1[C:80]([C:82]1[C:90]2[C:85](=[CH:86][CH:87]=[C:88]([Br:91])[CH:89]=2)[NH:84][CH:83]=1)=O)=O)C1C=CC=CC=1>>[Br:91][C:88]1[CH:89]=[C:90]2[C:85](=[CH:86][CH:87]=1)[NH:84][CH:83]=[C:82]2[CH2:80][C@H:76]1[CH2:77][CH2:78][CH2:79][N:75]1[CH3:73]

Participants

5

Reactant 4

HCID 249055-BromoindoleHCID 77993EletriptanHCID 11224090Phenylmethyl (2R)-2-((5-bromo-1H-indol-3-yl)carbonyl)-1-pyrrolidinecarboxylateHCID 540753983-(((2R)-1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethenyl)-1H-indole

Product 1

HCID 11185464(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole

Procedure

European Patent No. 0592438 describes the preparation of eletriptan by the catalytic reduction of (R)-5-(2-benzenesulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1 H-indole, which compound is prepared by (i) reacting N-benzyloxycarbonyl-D-proline acid chloride with 5-bromoindole in the presence of a Grignard reagent, (ii) reducing the resulting (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole to give (R)-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and (iii) reacting same with phenyl vinyl sulphone in the presence of a palladium catalyst, a triarylphosphine and a base.

Sources & evidence

ORD record
ord-1ae7cdfcbed54c7b9930293e43eaf366
Source dataset
uspto-grants-2007_10
Patent number
US07288662B2

Reaction notes

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