Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][OH:7].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:35]1[NH:36][C:37]2[CH:38]=[CH:39][CH:40]=[C:41]3[C:47](=[O:48])[NH:46][CH2:45][CH2:44][C:43]=1[C:42]=23.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:7][CH2:6][CH2:5][C:4]1[CH:3]=[C:2]([C:35]2[NH:36][C:37]3[CH:38]=[CH:39][CH:40]=[C:41]4[C:47](=[O:48])[NH:46][CH2:45][CH2:44][C:43]=2[C:42]=34)[CH:10]=[CH:9][CH:8]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
In a manner similar to that described for Example YY, 3-bromophenethyl alcohol (201 mg, 1.00 mmol), diboron pinacol ester (279 mg, 1.10 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (24 mg, 0.03 mmol), and potassium acetate (294 mg, 3.00 mmol), 2-bromo-3,4,5,6-tetrahydro-azepino[5,4,3-cd]indol-6-one (239 mg, 0.90 mmol), a second portion of 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (24 mg, 0.03 mmol), and sodium carbonate (2.5 mL of a 2.0 M aqueous solution, 5.00 mmol) were reacted to yield 2-[3-(2-hydroxy-ethyl)-phenyl]-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 135 mg (44%) as an off-white solid: m.p. 187.5-188.5° C.; 1H NMR (300 MHz, d6-DMSO) δ 2.82 (t, J=6.9 Hz, 2H), 3.12 (m, 2H), 3.39 (m, 2H), 3.69 (Abq, J=7.2, 5.1 Hz, 2H), 4.71 (t, J=5.1 Hz, 1H), 7.21 (t, J=7.8 Hz, 1H), 7.25 (d, J=7.2 Hz, 1H), 7.49 (m, 4H), 4H), 7.68 (dd, J=7.5, 0.9 Hz, 1H), 8.08 (br t, 1H), 11.55 (br s, 1H). MS (FAB, MH+): 307. Anal. (C19H18N2O2.0.1 H2O) C, H, N.
Sources & evidence
- ORD record
- ord-a37dcb191fe04535ab189b352e0824cf
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429578B2
Linked notes
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