Nitrogen → HCID 117700325, compound

HRID 589618Notes

Reaction equation

HRID 589618 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[C:7]([C:11]([OH:13])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:23].N#N>CO.C1(C)C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([S:14][C:6]2[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[NH:8][C:7]=2[C:11]([O:13][CH3:23])=[O:12])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 167693TrimethylsilyldiazomethaneHCID 71625402HCID 71625402, compound

Product 1

HCID 117700325HCID 117700325, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of impure 1g product (0.19 g, 0.59 mmol) in a mixture of methanol and toluene (6 mL, 1:2) was added TMSCHN2 (2.0 M solution in diethyl ether) (0.6 mL, 1.2 mmol) dropwise under N2. The reaction was allowed to warm to rt and stirred for 2 h. The reaction mixture was concentrated and purified by flash column chromatography eluting with a linear gradient ranging from 0 to 50% EtOAc-hexanes to provide 0.15 g (75%) of product 34 as an off white solid. 1H NMR (300 MHz, CDCl3) δ 3.93 (s, 3H), 6.88-6.95 (m, 1H), 7.06-7.16 (m, 5H), 7.45-750 (m, 1H), 9.22 (s, 1H). LC-MS (CI): m/z 336.0 [(M+H)+ C16H11ClFNO2S requires 335.02].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash column chromatography
  3. washeluting with a linear gradient

Sources & evidence

ORD record
ord-934d5b8034f14478821194130035fd5e
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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