Triphenylphosphine → N-tert-butyl-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-8-amine

HRID 1949860Notes

Reaction equation

HRID 1949860 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[C:9](I)=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[CH2:14][CH2:13][O:12][C:10]=2[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 57900152N-tert-butyl-5-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridin-2-amine

Product 1

HCID 57900131N-tert-butyl-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-8-amineYield 42%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Following Scheme 4, N-tert-butyl-5-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridin-2-amine was cyclized in the presence of palladium (II) acetate and triphenylphosphine to give N-tert-butyl-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-8-amine (42%). 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.04 (d, J=5.2, 1H), 6.81 (d, J=5.2, 1H), 6.07 (s, 1H), 4.59 (s, 1H), 4.35-4.29 (m, 2H), 3.21-3.07 (m, 2H), 1.42 (s, 9H). MS: (ESI+) 275.1

Sources & evidence

ORD record
ord-5ff60e33086246a88f66c245984d4cda
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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