Sodium Carbonate → 5-Benzo[1,3]dioxol-5-yl-3-furan-3-yl-1H-pyrrolo[2,3-b]pyridine

HRID 2114040Notes

Reaction equation

HRID 2114040 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:15]=[CH:14][O:13][CH:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.B(O)(O)[C:17]1[CH:22]=[CH:21][C:20]2[O:23][CH2:24][O:25][C:19]=2[CH:18]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[O:23]1[C:20]2[CH:21]=[CH:22][C:17]([C:2]3[CH:3]=[C:4]4[C:10]([C:11]5[CH:15]=[CH:14][O:13][CH:12]=5)=[CH:9][NH:8][C:5]4=[N:6][CH:7]=3)=[CH:18][C:19]=2[O:25][CH2:24]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 59811896H-Pyrrolo[2,3-b]pyridine, 5-bromo-3-(3-furanyl)-

Product 1

HCID 104702855-Benzo[1,3]dioxol-5-yl-3-furan-3-yl-1H-pyrrolo[2,3-b]pyridineYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Bromide 14 (17.6 mg, 0.07 mmol), 3,4-(methylenedioxy)phenylboronic acid (16.7 mg, 0.10 mmol), LiCl (8.4 mg, 0.20 mmol), PdCl2(Ph3P)2 (4.6 mg, 0.007 mmol) in 1 M aqueous Na2CO3 (0.17 mL, 0.17 mmol), PhMe (1.5 mL) and EtOH (1.5 mL) was heated at 105° C. After 5 h the mixture was allowed to cool to r.t. and then purified by PTLC with AcOEt:hexane=1:1 as eluent to afford azaindole 15 (15.2 mg, 76%) as a white solid. 1H NMR (400 MHz; CDCl3) δ 6.04 (s, 2H), 6.72 (dd, J=0.8 and 1.8 Hz, 1H), 6.94 (dd, J=7.9, 0.3 Hz, 1H), 7.08-7.12 (m, 2H), 7.48 (d, J=2.3 Hz, 1H), 7.54 (t, J=1.6 Hz, 1H), 7.82 (t, J=1.1 Hz, 1H), 8.15 (d, J=2.1 Hz, 1H), 8.52 (d, J=2.1 Hz, 1H), 9.61 (brs, NH).

Workup

  1. custompurified by PTLC with AcOEt

Sources & evidence

ORD record
ord-9306dbf9bfe048e7afcf144069eaec76
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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