Reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:33]1[NH:34][C:35]2[CH:36]=[CH:37][CH:38]=[C:39]3[C:45](=[O:46])[NH:44][CH2:43][CH2:42][C:41]=1[C:40]=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:8][C:5]1[CH:6]=[CH:7][C:2]([C:33]2[NH:34][C:35]3[CH:36]=[CH:37][CH:38]=[C:39]4[C:45](=[O:46])[NH:44][CH2:43][CH2:42][C:41]=2[C:40]=34)=[CH:3][CH:4]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
In a manner similar to that described for Compound YY, 4-iodophenol (220 mg, 1.00 mmol), diboron pinacol ester (279 mg, 1.10 mmol), 1,1′-bis(diphenyl phosphino)ferrocenedichloro palladium (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)ferrocene dichloropalladium (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-(4-hydroxy-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 39 mg (15%) as a beige solid: m.p. 300° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ 3.00 (m, 2H), 3.37 (m, 2H), 6.92 (d, J=8.7 Hz, 2H), 7.16 (t, J=7.8 Hz, 1H), 7.49 (m, 3H), 7.65 (dd, J=7.5, 0.9 Hz, 1H), 8.04 (br t, 1H), 9.73 (br s, 1H), 11.40 (br s, 1H). MS (electrospray, MH+): 279. Anal. (C17H14N2O2) C, H, N.
Sources & evidence
- ORD record
- ord-01063a03f97e4da8869143999e1966c7
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429578B2
Linked notes
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