Dichloromethane → HCID 68225765, compound

HRID 2036635Notes

Reaction equation

HRID 2036635 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17](I)=[C:18]([C@@H:20]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:21])[N:19]=2)[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>O1CCOCC1.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:18]([C@@H:20]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:21])[N:19]=2)[CH:16]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86658169HCID 86658169, compound

Product 1

HCID 68225765HCID 68225765, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a microwave vial was added phenylboronic acid (0.104 g, 0.852 mmol), (S)-benzyl 1-(6-fluoro-3-iodoimidazo[1,2-a]pyridin-2-yl)ethylcarbamate (0.250 g, 0.568 mmol), sodium carbonate (0.181 g, 1.74 mmol), and 1,1′-bis(diphenyl-phosphino)ferrocene palladium (II) chloride, 1:1 complex with DCM (0.023 g, 0.028 mmol) in dioxane (3.44 mL) and water (0.34 mL). The suspension was stirred at 110° C. under microwave irradiation for 2 h. Purification by MPLC (eluted with a gradient of 0-6% MeOH in DCM) afforded (S)-benzyl 1-(6-fluoro-3-phenylimidazo[1,2-a]pyridin-2-yl)ethylcarbamate as a brown oil. LC-MS (ESI) m/z 390.1 [M+H]+.

Workup

  1. customPurification by MPLC (
  2. washeluted with a gradient of 0-6% MeOH in DCM)

Sources & evidence

ORD record
ord-ae654c1fc8104fc1955d88d359938cb1
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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