Sodium Carbonate → Ammonia

HRID 450949Notes

Reaction equation

HRID 450949 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-f314cd21b92c4fbabacb99f2c3481d67
Source dataset
uspto-grants-2013_07
Patent number
US08486992B2

Reaction notes

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