2'-Methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acid → 2,3-Dihydro-1'-methyl-5-(2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl)spiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1741103Notes

Reaction equation

HRID 1741103 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:18]3[CH2:17][C:16]4[C:12]([CH:13]=[CH:14][N:15]=4)=[CH:11][C:10]=3[O:9][CH2:8]2)[CH2:4][CH2:3]1.[CH3:19][C:20]1[CH:25]=[C:24]([C:26]2[O:27][C:28]([CH3:31])=[N:29][N:30]=2)[CH:23]=[CH:22][C:21]=1[C:32]1[CH:37]=[CH:36][C:35]([C:38](O)=[O:39])=[CH:34][CH:33]=1.C(N1C2C(=CC(O)=C(Br)C=2)CC1)(=O)C>>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:18]3[C:10](=[CH:11][C:12]4[CH:13]=[CH:14][N:15]([C:38]([C:35]5[CH:34]=[CH:33][C:32]([C:21]6[CH:22]=[CH:23][C:24]([C:26]7[O:27][C:28]([CH3:31])=[N:29][N:30]=7)=[CH:25][C:20]=6[CH3:19])=[CH:37][CH:36]=5)=[O:39])[C:16]=4[CH:17]=3)[O:9][CH2:8]2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 186900662'-Methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acidHCID 219483801-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-oneHCID 701980042,3-Dihydro-1'-methylspiro[furo[2,3-f]indole-3,4'-piperidine]

Product 1

HCID 218338532,3-Dihydro-1'-methyl-5-(2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl)spiro[furo[2,3-f]indole-3,4'-piperidine]

Procedure

The title compound was prepared from 2,3-dihydro-1'-methylspiro[furo[2,3-f]indole-3,4'-piperidine] (D7) and 2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acid (D11) using a similar procedure to Example 8 (22%). This was converted to its oxalate salt, which crystallised from acetone/methanol as a white solid mp 234-237° C.

Workup

  1. customcrystallised from acetone/methanol as a white solid mp 234-237° C.

Sources & evidence

ORD record
ord-bc131c666a3848bda30bb7eada4c8076
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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