Water → HCID 21631643, compound

HRID 252811Notes

Reaction equation

HRID 252811 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[C:12]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:11][S:10][C:9]=1Br)([CH3:4])([CH3:3])[CH3:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:17]([O:16][C:14](=[O:15])[NH:13][C:12]1[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22])=[C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:10][CH:11]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 21631631HCID 21631631, compound

Product 1

HCID 21631643HCID 21631643, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a flame-dried round-bottom flask, tetrakis(triphenylphosphine) palladium (59 mg, 0.051 mmol) was added to a degassed solution of compound 58 (400 mg, 1.02 mmol) in DME (5 mL). Phenylboronic acid (186 mg, 1.53 mmol), water (2.5 mL), and Na2CO3 (324 mg, 3.06 mmol) were successively added, degassing and purging with nitrogen between each addition. The mixture was refluxed under nitrogen atmosphere for 3 h and partitioned between Et2O and water. The organic layer was dried over MgSO4 and concentrated in vacuum. The title compound 59 (398 mg, 100% yield) was obtained as a brown oil. 1H NMR: (CDCl3) δ(ppm): 7.51-7.31 (m, 6H), 1.54 (s, 18H). m/z: 413.5 (M+Na+). This procedure is essentially as described in Brugier et al., Tetrahedron, 56: 2985-2993 (2000), which is incorporated by reference in its entirety.

Workup

  1. customdegassing
  2. custompurging with nitrogen between each addition
  3. temperatureThe mixture was refluxed under nitrogen atmosphere for 3 h
  4. custompartitioned between Et2O and water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-3c30313f5255435883e0b3c4532ac30e
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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