2-Bromobenzonitrile → HCID 54768836, compound

HRID 1896900Notes

Reaction equation

HRID 1896900 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH2:4][CH2:3]1.BrC1C=CC=CC=1C#N.CC1(C)C(C)(C)OB(C2CCC3(OCCO3)CC=2)O1.[NH:44]1[CH2:47][CH:46]([NH:48][C:49](=[O:66])[CH2:50][NH:51][C:52]2[C:61]3[C:56](=[CH:57][CH:58]=[C:59]([C:62]([F:65])([F:64])[F:63])[CH:60]=3)[N:55]=[CH:54][N:53]=2)[CH2:45]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:10]([C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[CH:5]1[CH2:6][CH2:7][CH:2]([N:44]2[CH2:45][CH:46]([NH:48][C:49](=[O:66])[CH2:50][NH:51][C:52]3[C:61]4[C:56](=[CH:57][CH:58]=[C:59]([C:62]([F:63])([F:65])[F:64])[CH:60]=4)[N:55]=[CH:54][N:53]=3)[CH2:47]2)[CH2:3][CH2:4]1)#[N:11]

Participants

6

Reactant 5

HCID 162722-BromobenzonitrileHCID 36970768-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro(4.5)dec-7-eneHCID 5049666Sodium triacetoxyborohydrideHCID 21187698HCID 21187698, compoundHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 54768836HCID 54768836, compound

Procedure

Reaction of 2-(4-oxocyclohexyl)benzonitrile (prepared by the reaction of 2-bromobenzonitrile with 8-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,4-dioxa-spiro[4.5]dec-7-ene using the sequence described in Example 1 Step A-C) with N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide (as prepared in Example 1 Step G) in the presence of TEA and NaBH(OAc)3 as described in Example 1, Step H afforded the product.

Workup

  1. customafforded the product

Sources & evidence

ORD record
ord-5794ef33549f43c78195af73ffb1244b
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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