Sodium Carbonate → HCID 59198487, compound

HRID 1896533Notes

Reaction equation

HRID 1896533 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[N:10][CH:11]=[C:12]([C:15]#[N:16])[C:13]=3[S:14][C:4]=2[CH:3]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/B(O)O)=[CH:30][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:27][C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:2]2[CH:7]=[CH:6][C:5]3[C:8]4[C:9]([NH:17][CH2:18][C:19]5[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=5)=[N:10][CH:11]=[C:12]([C:15]#[N:16])[C:13]=4[S:14][C:4]=3[CH:3]=2)=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 5706776trans-2-(4-Fluorophenyl)vinylboronic acidHCID 591984657-Bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile

Product 1

HCID 59198487HCID 59198487, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 7-bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile (Example 12, Step 9) in 1-propanol (0.1 M) was added [(E)-2-(4-fluorophenyl)vinyl]boronic acid (1.5 equiv), 2.0 M aqueous Na2CO3 solution (2.5 equiv), and a 3:1 mixture of Ph3P:Pd(OAc)2 (0.1 equiv). The mixture was degassed and then stirred at 100° C. for 2.5 h, and was then partitioned between EtOAc/THF and H2O. The organic layer was washed with H2O and brine, and was then dried (MgSO4), filtered, and evaporated. The crude material was purified by flash chromatography, eluting with 1:1 Et2O:hexanes. The product was stirred with 1:10 EtOAc:hexanes containing trace acetone to yield the title compound as a pale yellow solid after filtration.

Workup

  1. customThe mixture was degassed
  2. customwas then partitioned between EtOAc/THF and H2O
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialwas then dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by flash chromatography
  8. washeluting with 1:1 Et2O
  9. stirringThe product was stirred with 1:10 EtOAc

Sources & evidence

ORD record
ord-be1583acaf064d7aabe6385f22142d36
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

Loading…