5-Bromo-2-fluoropyridine → 6-amino-5-bromo-2-(6-fluoropyridin-3-yl)-N-methylbenzofuran-3-carboxamide

HRID 595562Notes

Reaction equation

HRID 595562 reaction equation
[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12](=[O:15])[NH:13][CH3:14])=[C:7](B(O)O)[O:8][C:4]=2[CH:3]=1.Br[C:20]1[CH:21]=[CH:22][C:23]([F:26])=[N:24][CH:25]=1>O1CCOCC1.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]>[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12]([NH:13][CH3:14])=[O:15])=[C:7]([C:20]3[CH:25]=[N:24][C:23]([F:26])=[CH:22][CH:21]=3)[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 27831685-Bromo-2-fluoropyridineHCID 90332513(6-Amino-5-bromo-3-(methylcarbamoyl)benzofuran-2-yl)boronic acid

Product 1

HCID 903324186-amino-5-bromo-2-(6-fluoropyridin-3-yl)-N-methylbenzofuran-3-carboxamideYield 51.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of (6-amino-5-bromo-3-(methylcarbamoyl)benzofuran-2-yl)boronic acid (500 mg, 1.61 mmol) in dioxane/H2O (5 mL/0.5 mL) was added 5-bromo-2-fluoropyridine (420 mg, 2.42 mmol), Pd(dppf)Cl2(10 mg) and K3PO4.3H2O (855 mg, 3.21 mmol). The mixture was stirred at 50° C. for 10 h. The mixture was evaporated and washed with MeOH to obtain the yellow solid as the product of 6-amino-5-bromo-2-(6-fluoropyridin-3-yl)-N-methylbenzofuran-3-carboxamide (300 mg, yield: 51%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.76 (s, 1H), 8.44˜8.51 (m, 2H), 7.75 (s, 1H), 7.39˜7.42 (m, 1H), 7.09 (s, 1H), 5.71 (s, 2H), 2.88 (d, J=8.4 Hz, 3H). (M+H)+: 364/366.

Workup

  1. customThe mixture was evaporated
  2. washwashed with MeOH

Sources & evidence

ORD record
ord-22b03a191d554369bdcb7bbab97e3a25
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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