Potassium Carbonate → HCID 69326674, compound

HRID 2054592Notes

Reaction equation

HRID 2054592 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@@H:4]1[CH2:8][CH:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][N:5]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[CH:31]1[C:39]2[C:38]3[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=3[O:36][C:35]=2[C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.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>[CH3:1][O:2][C:3](=[O:30])[C@@H:4]1[CH2:8][CH:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:43]4[C:37]5[O:36][C:35]6[CH:34]=[CH:33][CH:32]=[CH:31][C:39]=6[C:38]=5[CH:40]=[CH:41][CH:42]=4)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][N:5]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2734328Dibenzofuran-4-boronic acidHCID 131726762HCID 131726762, compound

Product 1

HCID 69326674HCID 69326674, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4′-bromobiphen-4-yloxy)-N-tert-butoxycarbonyl-proline methyl ester (476 mg, 1 mmol), 4-dibenzofuranylboronic acid (222 mg, 1.05 mmol) and Pd(PPh3)4 (52 mg, 5% mol) in toluene (10 mL) and ethanol (2.5 mL) was heated until the solution became clear and subsequently treated with 2 M K2CO3 (1.5 mL). The reaction mixture was heated to reflux for 2 h, cooled to room temperature, diluted with ethyl acetate (100 mL). The organic layer was washed successively with 2% aq HCl and sat. aq NaCl, dried over MgSO4, filtered and concentrated. Purification by flash column chromatography (2-10% ethyl acetate in heptane) gave 4-(4′-dibenzofuran-4-yl-bipheny-4-yloxy)-N-tert-butoxycarbonyl-proline methyl ester (423 mg, 75%) as a foam. 1H NMR (CDCl3), δ 7.97 (m, 4H), 7.71 (dd, J=1, 8 Hz, 2H), 7.62 (m, 4H), 7.45 (m, 3H), 6.90 (dd, J=1, 9 Hz, 2H), 4.96 (m, 1H), 4.52 (m, 1H), 3.78 (m, 5H), 2.52 (m, 2H), 1.46 (s, 9H). LCMS 464 (M+−100).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. washThe organic layer was washed successively with 2% aq HCl and sat. aq NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (2-10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-2e5960a6aa7644fe8f211bb1178066fb
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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