4-Fluorophenylboronic acid → HCID 59784107, compound

HRID 2079768Notes

Reaction equation

HRID 2079768 reaction equation
[CH3:1][N:2]([C@@H:10]([CH3:39])[C:11]([NH:13][C@H:14]([C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C@H:21]1[C:26]([NH:28][C@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)=[O:27])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[F:40][C:41]1[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[F:40][C:41]1[CH:46]=[CH:45][C:44]([N:23]2[CH2:24][CH2:25][N:20]([C:18]([C@@H:14]([NH:13][C:11](=[O:12])[C@@H:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:7])([CH3:8])[CH3:6])[CH3:39])[CH:15]([CH3:17])[CH3:16])=[O:19])[C@H:21]([C:26]([NH:28][C@H:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:32][CH2:31][CH2:30]3)=[O:27])[CH2:22]2)=[CH:43][CH:42]=1

Participants

5

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 59784098HCID 59784098, compound

Product 1

HCID 59784107HCID 59784107, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Intermediate 7 (486 mg, 0.89 mmol), 4-fluorophenylboronic acid (625 mg, 4.47 mmol), Cu(OAc)2 (406 mg, 2.24 mmol) and TEA (451 mg, 4.47 mmol) are all weighed into a flask, then dissolved in dry CH2Cl2 (20 mL). This mixture is stirred for 24 h. at room temperature, at which point some of the desired product had formed by LCMS. A further portion of boronic acid (625 mg, 4.47 mmol) is added and the mixture allowed to stir for a further 24 h, making the desired product the major peak, along with unreacted starting material. This reaction mixture is concentrated under reduced pressure, then loaded directly onto a plug of silica which is eluted with 10% Et2O/CH2Cl2 to isolate the desired product. Unreacted starting material remains at the column baseline under these conditions. The title compound is isolated as a off-white foam (188 mg, 33% yield): 1H NMR δ (CDCl3) 6.92-7.42 (m, 8H), 6.74 (v br s, 1H), 6.09 (br d, J=8.4 Hz, 1H), 3.97-5.27 (br m, 6H), 3.35-3.56 (br m, 2H), 2.62-3.16 (br m, 7H), 1.65-2.14 (m, 5H), 1.47 (s, 9H), 1.31 (br d, J=7.1 Hz, 2H), 1.14 (br d, J=7.1 Hz, 1H), 0.98 (brt, J=7.3 Hz, 2H), 0.79 (br d, J=6.7 Hz, 2H), 0.61 (br d, J=6.7 Hz, 2H); LCMS (APCl+) 639.4 (MH+, 100%).

Workup

  1. customall weighed into a flask

Sources & evidence

ORD record
ord-372e9e79912d4d54bca7bb4100e053da
Source dataset
uspto-grants-2011_04
Patent number
US07932255B2

Reaction notes

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