Sodium Carbonate → HCID 86585372, compound

HRID 1168903Notes

Reaction equation

HRID 1168903 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].Br[C:20]1[CH:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2/[CH:32]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:23]=[CH:24][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:24]2[CH:23]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3/[CH:32]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:21]=[CH:20][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acidHCID 86585373HCID 86585373, compound

Product 1

HCID 86585372HCID 86585372, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

As described in Example 1 (step 1), a mixture of 2-(phenylmethoxy) benzeneboronic acid (545 mg, 2.39 mmol), ethyl (E)-3-[2-(3-bromophenyl)phenyl]prop-2-enoate bromide (390 mg, 1.18 mmol) of Example 1 (step 2), 2M Na2CO3 (3.5 mL) and (Ph3P)4Pd (66 mg, 0.06 mmol) in DME (7 mL) was heated to 80° C. for 2 h. Purification by flash chromatography (Tol) provided the desired material as a yellow solid (485 mg, 95%). 1H NMR (acetone-d6) δ 2.04 (3H, t), 4.12 (2H, q), 5.16 (2H, s), 6.51 (1H, d), 7.07 (1H, td), 7.20 (1H, dd), 7.2-7.4 (8H, m), 7.4-7.5 (4H, m), 7.6-7.7 (2H, m), 7.79 (1H, d) and 7.89 (1H, dd).

Workup

  1. customPurification by flash chromatography (Tol)

Sources & evidence

ORD record
ord-c93f4bd1516b45a39b1ef61a7b680b3e
Source dataset
uspto-grants-2003_09
Patent number
US06627656B2

Reaction notes

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