Sodium Carbonate → Ammonia

HRID 2387689Notes

Reaction equation

HRID 2387689 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([CH3:32])([CH3:31])[CH2:14][CH2:15][C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]#[N:18])[CH2:9][CH2:8]1.[OH:36][C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][CH:42]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.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]>[NH3:10].[OH:36][C:37]1[CH:42]=[C:41]([C:2]2[CH:35]=[CH:34][CH:33]=[C:4]([CH2:5][O:6][CH:7]3[CH2:12][CH2:11][N:10]([C:13]([CH3:31])([CH3:32])[CH2:14][CH2:15][C:16]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:17]#[N:18])[CH2:9][CH2:8]3)[CH:3]=2)[CH:40]=[CH:39][CH:38]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 59423969HCID 59423969, compound

Product 2

HCID 222AmmoniaHCID 59423956HCID 59423956, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1,1′-Bis (diphenylphosphino)ferrocenedichloro palladium(II) (8 mg, 0.09 mmol) was added to a suspension of the product of example 87 (100 mg, 0.19 mmol), 3-hydroxyphenylboronic acid (52 mg, 0.038 mmol) and sodium carbonate (40 mg, 0.038 mmol) in tetrahydrofuran (5 mL) and water (1 mL) and the mixture was heated at 60° C. for 12 hours. The suspension was allowed to cool to room temperature and then evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 99:1:0 to 98:2:0.2, to give the title compound as a gum in 72% yield.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated to dryness under reduced pressure
  3. customThe residue was purified by chromatography on silica gel
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-0e706b6a75124728b578aee21d06f168
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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