Dimethylformamide → HCID 84734218, compound

HRID 2277611Notes

Reaction equation

HRID 2277611 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([CH:11]1[CH2:13][CH2:12]1)[NH2:10].CCN(C(C)C)C(C)C.CN([CH:26]=[O:27])C>CCOC(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:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[C:26](=[O:27])[NH:10][CH:9]2[CH:11]1[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 71743654HCID 71743654, compound

Product 1

HCID 84734218HCID 84734218, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (2-bromo-5-chlorophenyl)(cyclopropyl)methanamine (2 g, 7.7 mmol), Pd(dppf)Cl2 (0.2 g), DIPEA (3 g, 23.1 mmol) in 20 mL of DMF was heated in an autoclave at 130° C. under 2 MPa of CO (g) for 16 hours. After the reaction, the mixture was diluted with AcOEt (150 mL) and washed with brine (30 mL×3). The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product which was purified by chromatography to give title compound (1.1 g, yield 68.7%) as a yellow solid. MS: 207.9 (M+H+, 1C1).

Workup

  1. customAfter the reaction
  2. washwashed with brine (30 mL×3)
  3. customThe organic layer was dried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas purified by chromatography

Sources & evidence

ORD record
ord-8c7b21be93a04347b293600d6ec73d8c
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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