Dimethylformamide → Benzaldehyde, 3-(1-methylethoxy)-5-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-

HRID 1625458Notes

Reaction equation

HRID 1625458 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.[CH:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[C:26]([O:28][CH:29]([CH3:31])[CH3:30])[CH:27]=1)=[O:21].CN(C)C=O.C(=O)(O)[O-].[Na+]>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].C(Cl)Cl>[CH:29]([O:28][C:26]1[CH:27]=[C:22]([CH:23]=[C:24]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[N:4]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:3]=2)[CH:25]=1)[CH:20]=[O:21])([CH3:31])[CH3:30]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 162180583-Formyl-5-isopropoxyphenylboronic acidHCID 455881343-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 73014036Benzaldehyde, 3-(1-methylethoxy)-5-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-Yield 71.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Solvent

Procedure

3-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (750 mg, 0.0022 mol) and 3-formyl-5-isopropoxyphenylboronic acid (510 mg, 0.0024 mol) were dissolved in N,N-Dimethylformamide (10 mL, 0.2 mol) and then added 1.2 M of Sodium bicarbonate in water (6 mL) and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (20 mg, 0.00002 mol). Flushed with nitrogen and The reaction was microwaved on 50 watts, 120° C. for 15 minutes. LC-MS showed complete reaction (1.99 min, ES+/421.07) Worked up with DCM and water. Dried over MgSO4. Purified on silica gel column with 0-100% EtOAc to give the desired product as a yellow syrup (665 mg, 71%) MS (ES+) m/z 421.07 (M+1). 1H NMR (CDCl3, 400 MHz): ™10.03 (s, 1H), 8.50 (d, 1H), 8.26 (d, 2H), 8.13 (d, 1H), 7.97 (s, 1H), 7.66 (s, 1H), 7.60 (t, 1H), 7.51 (t, 2H), 7.38 (s, 2H) 7.26 (dd, 1H), 4.72 (qd, 1H), 1.41 (d, 6H)

Workup

  1. customFlushed with nitrogen
  2. customThe reaction was microwaved on 50 watts, 120° C. for 15 minutes
  3. customreaction (1.99 min, ES+/421.07)
  4. dry with materialDried over MgSO4
  5. customPurified on silica gel column with 0-100% EtOAc

Sources & evidence

ORD record
ord-d9056c5a2a9947279384cc98c40648a0
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

Loading…