6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile → HCID 74983276, compound

HRID 1915950Notes

Reaction equation

Br[C:2]1[S:3][C:4]([NH:33]C(=O)OC(C)(C)C)=[C:5]([C:7](=[O:32])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:31])[C:13]=2[N:14]2[CH2:20][CH2:19][C@@H:18]([NH:21]C(OC(C)(C)C)=O)[CH2:17][C:16]([F:30])([F:29])[CH2:15]2)[N:6]=1.CC1(C)C(C)(C)OB([C:49]2[N:54]=[C:53]([C:55]#[N:56])[CH:52]=[CH:51][CH:50]=2)O1>>[NH2:33][C:4]1[S:3][C:2]([C:49]2[CH:50]=[CH:51][CH:52]=[C:53]([C:55]#[N:56])[N:54]=2)=[N:6][C:5]=1[C:7]([NH:8][C:9]1[CH:10]=[N:11][N:12]([CH3:31])[C:13]=1[N:14]1[CH2:20][CH2:19][C@@H:18]([NH2:21])[CH2:17][C:16]([F:30])([F:29])[CH2:15]1)=[O:32]

Participants

Reactant 2

HCID 177504686-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile

HCID 86680147tert-butyl N-[2-bromo-4-[[5-[(5R)-5-(tert-butoxycarbonylamino)-3,3-difluoro-azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate

Product 1

HCID 74983276HCID 74983276, compound

Procedure

Following the procedures in Example 428, tert-butyl N-[2-bromo-4-[[5-[(5R)-5-(tert-butoxycarbonylamino)-3,3-difluoro-azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate was reacted with 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile to give 461. LCMS (ES+) m/z 474 (M+1)

Sources & evidence

ORD record: ord-26a4aeba265d42758c3760b4244b1a16
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614206B2

Reaction notes

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