2-Iodobenzoic acid → HCID 86671457, compound

HRID 1530490Notes

Reaction equation

HRID 1530490 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([CH2:23][OH:24])=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:3].IC1C=CC=CC=1C(O)=O>CCOC(C)=O>[CH3:3][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([CH:23]=[O:24])=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:1]

Participants

4

Reactant 2

HCID 69412-Iodobenzoic acidHCID 68313089HCID 68313089, compound

Product 1

HCID 86671457HCID 86671457, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of {4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}methanol (1.30 g, 4.00 mmol) in EtOAc (100 mL) was added 2-iodobenzoic acid (4.48 g, 16.0 mmol). The mixture was heated at 80° C. overnight. The solid was filtered, the filtrate was concentrated and purified by column chromatography on silica gel eluting with a 20% gradient of EtOAc in petroleum ether to afford 4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-13-carbaldehyde (800 mg, 62% yield) as yellow solid. LCMS (ESI) m/z: 324.2 [M+H+].

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by column chromatography on silica gel eluting with a 20% gradient of EtOAc in petroleum ether

Sources & evidence

ORD record
ord-cbf9ca44df2740ec8aa19e6bc1e6a76b
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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