Water → HCID 131736801, compound

HRID 1486711Notes

Reaction equation

CB(O)O.[C:5]([O-])([O-])=O.[Na+].[Na+].[C:11]([NH:15][C:16]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[C:27](Br)[CH:26]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].O>C1(C)C=CC=CC=1.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.CCOC(C)=O>[C:11]([NH:15][C:16]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[C:27]([CH3:5])[CH:26]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

Methylboronic acid (23.2 mg, 0.377 mmol) and a solution of 2 M Na2CO3 (0.088 mL, 0.502 mmol) is added to a solution of 1-(3-bromo-5-nitro-benzyl)-piperidine-4-carboxylic acid tert-butylamide BB-10a (100 mg, 0.251 mmol) in anhydrous toluene (3 mL) The mixture is purged under argon for 15 min. Tetrakis(triphenylphosphine)palladium (0) (58 mg, 0.0502 mmol) is added and the mixture is heated to 100° C. overnight. Water (10 mL) and AcOEt (10 mL) are added and the aqueous phase is extracted twice with AcOEt (10 mL). The combined organic phases are dried over MgSO4, filtered and concentrated under reduced pressure. The title compound is obtained by prep. LC-MS F as a colorless powder (61 mg, 73%); LC-MS A: tR=0.63 min; [M+H]+=334.24.

Workup

customis purged under argon for 15 min
extractionthe aqueous phase is extracted twice with AcOEt (10 mL)
dry with materialThe combined organic phases are dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-03c2a160ff9c4d33be6a5a2a4a53f3ed
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428456B2

Reaction notes

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