Triphenylphosphine → 5-(12-fluoro-6,7-dihydro-5H-pyrido[2',3':3,4]azepino[1,2-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595742Notes

Reaction equation

HRID 595742 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]1[N:16]=[C:15]([C:17]3[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:40])=[O:39])=[CH:19][C:20]4[O:24][C:23]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=4[CH:36]=3)[CH:14]=[CH:13][C:12]=1[CH2:43][CH2:44][CH2:45]O)[NH:6]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:11]4[N:16]=[C:15]([C:17]5[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:39])=[O:40])=[CH:19][C:20]6[O:24][C:23]([C:25]7[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=7)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=6[CH:36]=5)[CH:14]=[CH:13][C:12]=4[CH2:43][CH2:44][CH2:45][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 903336015-(6-(4-fluoro-1H-indol-2-yl)-5-(3-hydroxypropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 903338445-(12-fluoro-6,7-dihydro-5H-pyrido[2',3':3,4]azepino[1,2-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(6-(4-fluoro-1H-indol-2-yl)-5-(3-hydroxypropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (153 mg, 0.237 mmol) and triphenylphosphine (62.2 mg, 0.237 mmol) in THF was added diisopropyl azodicarboxylate (0.046 mL, 0.237 mmol). The resultant mixture was stirred at ambient temperature for 10 h then was concentrated in vacuo and the residue purified by silica gel column chromatography using a step gradient of 0-50-100% EtOAc/Hexanes as eluent. 1H NMR δ (ppm) (CHCl3-d): 8.07 (1H, s), 8.02 (2H, dd, J=8.61, 5.32 Hz), 7.75 (1H, d, J=7.78 Hz), 7.70 (1H, s), 7.60 (1H, d, J=7.77 Hz), 7.26˜7.0 (4H, m), 7.09 (1H, s), 6.85˜6.81 (1H, m), 5.98 (1H, br s), 4.23 (2H, t, J=6.66 Hz), 3.35 (3H, s), 3.03 (3H, d, J=4.90 Hz), 2.85 (2H, t, J=7.00 Hz), 2.80 (3H, s), 2.47˜2.42 (2H, m), MS (M+H)+: 627.

Workup

  1. concentrationthen was concentrated in vacuo
  2. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3fb3e3b5efb42868e1d52b44f02c8d4
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

Loading…