Sodium Carbonate → HCID 44476773, compound

HRID 2192540Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[C:17]2[C:12](=[C:13]([C:18]3[N:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH:30]([CH3:32])[CH3:31])=[C:25]([Cl:33])[CH:24]=4)[O:20][N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1.OB(O)[C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=1)[C:39]([OH:41])=[O:40]>COCCOC.C(O)C.O.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]>[Cl:33][C:25]1[CH:24]=[C:23]([C:21]2[O:20][N:19]=[C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[C:17]4[C:12]=3[CH:11]=[CH:10][N:9]=[C:8]4[C:36]3[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=3)[C:39]([OH:41])=[O:40])[N:22]=2)[CH:28]=[CH:27][C:26]=1[O:29][CH:30]([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium carbonate (85 mg) and PdCl2(dppf)2 (50 mg) were added sequentially to a suspension of 1-bromo-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline (D40; 180 mg) and 3-(dihydroxyboranyl)benzoic acid (Aldrich; 99 mg) in 1,2-dimethoxyethane (DME; 2 ml), ethanol (1 ml) and water (1 ml). The resulting suspension was heated to 80° C. and stirred for overnight. The solvent was evaporated in vacuo and the residue was purified by MDAP to give the title compound (20 mg). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 4.90 (1H, m), 7.48 (1H, d), 7.73 (1H, t), 7.86 (1H, t), 7.95 (1H, dd), 8.19 (5H, m), 8.60 (1H, dd), 8.78 (2H, m), 13.17 (1H, br s).

Workup

customThe solvent was evaporated in vacuo
customthe residue was purified by MDAP

Sources & evidence

ORD record: ord-b0db569870d446d09fba6ae8d00c2206
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329730B2

Reaction notes

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