Dichloromethane → HCID 178458278, compound

HRID 1518135Notes

Reaction equation

HRID 1518135 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]([C:9]3[CH2:13][C:12]4([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)[O:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1.[CH3:21][C:22]1([CH3:32])[O:26]B(O)[C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]1=2.C(Cl)Cl>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]>[O:11]1[C:12]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:13][C:9]([C:7]2[NH:6][C:5]3[CH:19]=[CH:20][C:2]([C:24]4[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=4[C:22]([OH:26])([CH3:32])[CH3:21])=[CH:3][C:4]=3[N:8]=2)=[N:10]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 442289743,3-Dimethyl-1,3-dihydro-2,1-benzoxaborol-1-olHCID 178419324HCID 178419324, compound

Product 1

HCID 178458278HCID 178458278, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Using the procedure for step D in Example 1, the title compound was prepared from 3-(5-bromo-1H-benzimidazol-2-yl)-1-oxa-2-aza-spiro[4.5]dec-2-ene (150 mg, 0.449 mmol, as prepared in the previous step) and 3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol (2.0 eq., 145 mg, 0.898 mmol, prepared as described in US2007/259936) and (dppf)PdCl2.DCM (0.10 eq., 36.6 mg, 0.045 mmol) in 9% yield (16.4 mg). 1H-NMR (400 MHz, d4-MeOH) δ: 7.82 (dd, J=8.1, 1.3 Hz, 1H), 7.53-7.68 (m, 1H), 7.47 (br. s., 1H), 7.35 (td, J=7.6, 1.6 Hz, 1H), 7.19-7.24 (m, 2H), 7.05 (dd, J=7.6, 1.3 Hz, 1H), 3.28 (s, 2H), 1.69-1.90 (m, 6H), 1.46-1.65 (m, 4H), 1.33 (s, 6H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C24H27N3O2: 390.2 (M+H). found: 390.4.

Sources & evidence

ORD record
ord-92d3acf84a8940669a2fd122b4e1ce37
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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