Sodium Hydroxide → HCID 66841471, compound

HRID 1929210Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=O)[NH:6]2.CC[N:16](C(C)C)C(C)C.[C:23]([O:27][C:28](=[O:36])NC1CCNCC1)([CH3:26])([CH3:25])[CH3:24].C1CN([P+](ON2N=[N:61][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60]C2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:23]([O:27][C:28]([N:61]1[CH2:56][CH2:57][CH:58]([NH:16][C:11]([C:5]2[NH:6][C:7]3[C:3]([CH:4]=2)=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=3)=[O:13])[CH2:59][CH2:60]1)=[O:36])([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Bromo-1H-indole-2-carboxylic acid (3 g, 12.5 mmol) is dissolved in 30 ml of DMF and the solution is cooled to 0° C. After addition of Huenigs base (6.4 ml, 37.5 mmol), the mixture is stirred for 15 min. Then piperidin-4-yl-carbamic acid tert-butyl ester 3 (2.5 g, 12.5 mmol) is added, followed by PyBOP (7.2 g, 13.7 mmol). The reaction mixture is stirred for 18 h at room temperature. Then ethyl acetate is added and conc sodium hydroxide until a pH of 11 is reached. The organic layers are washed with brine, dried over sodium sulphate and evaporated. The crude product is further purified by flash-chromatography (silica gel, ethyl acetate/cyclohexane 1:1)

Workup

stirringThe reaction mixture is stirred for 18 h at room temperature
washThe organic layers are washed with brine
dry with materialdried over sodium sulphate
customevaporated
customThe crude product is further purified by flash-chromatography (silica gel, ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record: ord-e7f75a511a774fce9a01bf13b30d11fd
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183366B2

Reaction notes

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