Ammonium Chloride → HCID 86724297, compound

HRID 594896Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](I)[C:3]=1[C:4]#[N:5].C([Li])CCC.[Br:16][C:17]1[CH:18]=[C:19]2[C:26](=[CH:27][CH:28]=1)[O:25][CH2:24][C:21]1([CH2:23][CH2:22]1)[C:20]2=[N:29]S(C(C)(C)C)=O.[NH4+].[Cl-]>C1COCC1>[Br:16][C:17]1[CH:18]=[C:19]2[C:20]3([C:6]4[C:3](=[C:2]([F:1])[CH:9]=[CH:8][CH:7]=4)[C:4]([NH2:5])=[N:29]3)[C:21]3([CH2:22][CH2:23]3)[CH2:24][O:25][C:26]2=[CH:27][CH:28]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-fluoro-6-iodobenzonitrile (1560 mg, 6.32 mmol) in THF (16 mL) at −78° C. was added n-butyllithium (2.64M solution in n-hexane, 2.39 ml, 6.32 mmol) dropwise. The mixture was stirred for 0.5 hour at −78° C. and to the solution was added a solution of N-(6-bromo-4H-spiro[chromene-3,1′-cyclopropan]-4-ylidene)-2-methylpropane-2-sulfinamide (1500 mg, 4.21 mmol) in THF (5 mL). The mixture was stirred for 1 hour at −78° C. and overnight at room temperature. To the mixture was added saturated aqueous NH4Cl. The mixture was extracted with EtOAc and the organic layer was concentrated in vacuo. The residue was purified by silica gel chromatography (hexane/AcOEt=100:0-0:100, then CHCl3:MeOH=85:15) to give 6′-bromo-4″-fluorodispiro[cyclopropane-1,3′-chromene-4′,1″-isoindol]-3″-amine (469 mg).

Workup

stirringThe mixture was stirred for 1 hour at −78° C. and overnight at room temperature
extractionThe mixture was extracted with EtOAc
concentrationthe organic layer was concentrated in vacuo
customThe residue was purified by silica gel chromatography (hexane/AcOEt=100:0-0:100

Sources & evidence

ORD record: ord-ba82c332da50432e91397db0ed83203d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242973B2

Reaction notes

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